A facile enzymatic process for the preparation of ibuprofen ester prodrug in organic media

A novel glucopyranoside derivative of ibuprofen, ibuprofen methyl α-d-glucopyranoside ester was synthesized via immobilized lipase-catalyzed esterification between racemic ibuprofen and methyl α-d-glucopyranoside in non-aqueous medium. An appropriate product concentration (4.6 mg ml−1) was achieved by optimization of reaction conditions, such as solvent type, reaction temperature, enzyme concentration and initial concentration of substrates. Comparing with the parent drug ibuprofen in physicochemical properties, the glucopyranoside derivative of ibuprofen has better hydrophilicity. The chemical structure of the ibuprofen ester was confirmed to be methyl 6-O-(2′-(4′-isobutylphenyl) propionyl) α-d-glucopyranoside.